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Monday, September 28, 2009

Savouring Vanille Galante by Hermès now that the weather is getting cooler again, I am struck by its "solar" effect, a warming, "open", bright effect that is rendered through the use of salicylates: benzyl salicylate, cis 3 hexenyl salicylate, and iso amyl salicylate. To the perfume student these molecules present fascinating facets on the path of creation because salicylates encompass complimentary aspects and aid diffusion, making fragrances open up and "expand" in a sunny, exhilarating way. Gardenia, tiaré, and frangipani accords are usually built on salicylates and their summery vibe warms our heart even in winter. In this article we're going to occupy ourselves with the ones which are most often used in fine fragrances.

Benzyl Salicylate (benzyl ortho hydroxy benzoate) is an almost colourless liquid that has a mild balsamic, sweetly floral note possessing excellent blending capabilities. Often used ~like foundation is for make-up~ as a base for heavy florals such as ylang, gardenia, jasmine, lily etc. It is also used in functional products such as soap, shampoo and fabric softener. Along with Methyl Salicylate, salicylates “turn the most banal floral composition into a real perfume, with majestic weight and sweep” divulges Luca Turin. However some people are anosmic to it, including some perfumers. Guy Robert could not smell benzyl salicylate at all, but could instantly recognize its presence in perfume: “I recognize it as if it were a friend seen from behind in a crowd, by the cut of his shoulders”. Indeed in the words of nose Bernand Chant “it produces a diffusing, blooming effect very pleasing to the public”. Many orchid fragrances are built on salicylates, while the mysterious emerald glow of the vintage Je Reviens is also due to them. Coupled with eugenol and isoeugenol, the effect becomes almost carnation-like with its clove tint. The magic of benzyl salicylate can be best experienced in the archetypal floral bouquet of L’air du Temps featuring an overdose of the ingredient. Its progeny included Wind Song, Norell, Estée, Charlie, even Angel! However the recent restrictions on the use of benzyl salicylates have taken their toll on many floral fragrances, L’air du Temps included, which simply do not smell as they used to.

Methyl salicylate (salicylic acid methyl ester or oil of wintergreen ~because it is present in lots of evergreens such as birch and also rhododendrons~ and commonly featured in arthritis and muscle body rubs but also in Life Savers) has a green glow with camporeous aspects. Naturally occuring in tuberose, jasmine and hyacinth absolutes, as well as ylang ylang and neroli oil, it provides that characteristic eucalyptus-mint nuance of Tubéreuse Criminelle and to a lesser degree Carnal Flower. It is also a big ingredient in birch tar, used in Russia in treating leather and therefore associated with Cuir-de-Russie-themed fragrances, modernly interpreted in Dzing! and Bulgari Black. Also present in cassie absolute, so it seems to be the bridge between those and Une Fleur de Cassie; the connection being that acacia bark (the inspiration behind the latter) was also used in treating leather, in France.

Amyl salicylate (pentyl ortho hydroxy benzoate) is a colourless liquid related to coumarin olfactorily, frequently used to round off a composition and fix fine fragrance (floral or non-floral) even though not a constituent of volatile oils. The molecule is also referenced as orchidee, trefle or trefol due to its orchid-like lightly sweet floral and herbaceous-green aroma and its inclusion in L.T. Piver's 1898 mythical Le Trèfle Incarnat. A tiaré accord built on amyl salicilate is used in the Dior Bronze range to impart the lightly powdery floral nuance which serves as a reminder of beloved products of sunbathing (see below). Chances are you've smelled amyl salicylate in your favourite shampoo, deo, hair spray or fabric softener too as it is so prevalent in those products or used it in your anti-rheumatism prescription.

Ylang ylang (cananga odorata), a very frequent floral essence in perfumery and a constituent inVanille Galantewhich prompted these syllogisms in the first place, naturally encompasses salicylates and eugenol (a spicy ingredient); the former in the form of benzyl salicylate is the basic ingredient in the Ambre Solaire suntan lotion, with its white flowers tinge, which is synonymous with summer vacations to many Europeans (The ingredient first entered the composition for its sunscreening properties and later overstayed thanks to the fond reactions of users to its smell). Even the humble aspirin is a product of salicylates. The magic of salicylates is that they creep up on you from the most unlikely places!

The Piver scent is intriguing; when I was in Grasse recently I visited the Musee International de la Parfumerie and of course they have a charming stylised mock-up of a late 19th/early 20th century Piver shop.

For sunscreens I would add also ethylhexyl salicylate (=octyl) that is very common today and has also a very mild note.Methyl salicylate was used a lot in pharmacy in basic products (is this the reason we feel "une odeur médicinale"?). Also with other salicylates and methyl blue is used to denaturate the alcohol (alcool sanitaire).Another perfume very rich in salicylates is Fidji (Guy Laroche).

Wonderful post, as usual. Natural perfumers often look into the chemistry of the elusive flower they wish to recreate, eg gardenia, and play with accords of other aromatics that contain the major components.

The anosmia is strange. I often hear more about musk anosmia. I wonder what other scent-specific anosmias there are out there. I and other perfumers I've spoke with often have temporary anosmias due to working on mods. After a while, our noses just don't smell an important ingredient. Some time passes, we stay away from the ingredient, and the ability to sense it returns.

I have severe salicylate allergies, and this is something that some readers might want to be aware of. It is something that can be life-threatening. You can find a lot of information on the web about this. I love perfume too but need to be careful about ones I use. People (like myself) often become aware of the problem when they begin to experience severe reactions to aspirin. In my own case, ingesting the salicylates is a lot worse than having skin contact, but this may differ from person to person.

Intrigued and edified by your post (as so often happens)...further piqued by Octavian's comment about Fidji...off to take a hit from my mini to see if I can start isolating "salycilate."

Meanwhile, this collection of thoughts reminds me that I recently got a "vintage" bottle of L'Origan...'50's or '60's? not as old as another I've tried...and the first thing I thought upon the opening was sunscreen from my childhood. At the time, I thought that it had something to do with the topnotes going off, but now I wonder...

Thanks for the fun brain hum. Next time I enjoy some birch tar in a fragrance, I'll raise a toast to methyl salicylate. Who knew?

Thank you so much for your explanation of salicylates. I searched for this information to little avail when Vanille Galante was introduced. I found very little and nothing as good as what you have written here.

Very often the chemical deconstruction of perfumes makes my eyes glaze over, but you create such fascination as you weave the chemicals into a web of connections, feelings, and memories. Very nicely done!

I have been searching for the Piver for a long time, something might come up, we'll see. I recall we had discussed the museum, it's a charming idea and I would love them to attempt a recreation Osmotheque-style.

of course octyl seems to be a default ingredient nowadays in sunscreens. I almost invariably start wondering about stability upon reading sunscreen labels (avobenzone destabilizing, octocrylene being present or not, etc etc.) rather than paying attention to smell but you're absolutely right, it does have a mild smell.

In my mind, I have no doubt that "the reverse association" is very much true with medicinal smells: some things are used in medicine and therapeutic preparations therefore we associate the smell with the products used and not the ingredients that bear the smell in the first place. Same with mothballs and with bug sprays, I find. Most people are intimately familiar with those finished products and not with the raw materials (camphor, wintergreen etc), therefore the association in perfume works that way: It's awfully interesting, isn't it? I find it especially illuminating when it is described in a negative light, when people use them as ref points to avoid in fragrances. (Because obviously medicinal smells might provoke bad images/associations with illness, pain and distraught)

Fidji: great addition!! How did I manage to forget this one? It's one of Catapano's creations, eh? I very much like it, although I hear it's changed too (my last bottle is from 5 years ago or so)

It's definitely true that when recreating scents one needs to lean on the bare building blocks and try to re-assemble. Not an easy feat!

Re: anosmia. I can't say that benzyl salicylate is much of an odour to me, the same way that Iso-E Super is not. They have a hazy effect to my nose, at a loss to describe them in specific terms. So I might be hyposmic to them? :/

But regarding musk anosmia I haven't encountered it yet and I am a musk fiend, who likes almost anything musky (be it clean or dirty). The seperate musks (synthetic and real) I have smelled, I smell them all right, even though I have my favourites and not-so-favourites among them. What's the percentile of the population who doesn't have musk anosmia to any of the musks used?

I understand that the aspirin salycilate is not for everyone and it is quite serious (my sympathies). However the percentages of salicylates in perfumes are quite miniscule and not to be ingested. I would be much more concerned about sunscreens really, which are supposed to be used every day and in large amounts. It's good to make an informed choice at any rate, so thanks.

so happy the post strikes a chord with you! The sunscreen memory is so potent with so many I think it needed to be addressed in that light. Many people ask what's the difference between Ambre Solaire and Coppertone in terms of smell, and here it is! (Coppertone is much more coconutty of course)

I'm humanities too! Lots of perfumistas are aren't they? interesting! I was always dreadful at chemistry, if only I had realised my perfume passion earlier i would have been a lot more engaged. It's all down to how they teach these things isn't it.

I (personally) think it's lots of perfumistas who are vocal about it that are in Humanities ;-) I am sure there are hundreds of people appreciating smells who just don't have the inclination to talk about it. I was pretty good at chemistry (and maths) and recall being fascinated about how things work. But the different teachers do make a difference, no question about it. I was lucky in having good ones in those subjects.

Don't really think so, if that helps. The main constituents in oudh are sesquiterpenes and phenylethyl chromones according to my research, as well as protein kinases (non olfactory elements).Take a look at this:http://bmcgenomics.biomedcentral.com/articles/10.1186/1471-2164-14-227

But salicylates (benzyl salicylate especially) may be used in perfume formulae WITH oudh, that's unrelated but influencing one's perception of the note. Maybe?

Elena Vosnaki is executive editor of Fragrantica.gr, the leader in fragrance information in Greek, as well as a senior editor for the top english-speaking Fragrantica.com webzine.

Vosnaki has been Fragrance Expert on About.com and the Perfume History Curator of the Be Open Foundation exhibitionThe Garden of Wonders, A Journey in Scents in Milan. Her writing has been twice shortlisted in the FIFI Editorial Excellence Awards and is extensively quoted by authors. She is an evaluating expert on Osmoz.com.

Perfume Shrine is an award winning blog of 1000s of fragrance reviews (modern, niche, classic, vintage), articles on perfume history and aroma materials, comparisons of scents, interviews with perfumers & the fragrance industry, perfume shopping as well as scented travel memoirs, fine cuisine, tips on building a fragrance wardrobe and musings about the pleasures of the senses.